Never Have I Ever: Jerked Off With a Stranger via Webcam

Here’s What It’s Like to Get Off With a Random Person Online

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Thanks to the internet, you can pay a stranger to watch you jerk off.

By hiring a cam girl who consents to your wishes, you can fulfill your fantasy of masturbating as a beautiful woman watches. After all, some men enjoy the feeling of power that comes with jerking off in front of someone.

It’s their dick, dammit, and this lovely lady is going to watch it explode. Others enjoy the humiliation aspect, seeking a professional dominatrix to laugh at how pathetic they look as they stroke themselves to orgasm.

Regardless of how or why you like it, odds are you’re curious about what jerking off with a stranger through a webcam is like.

We asked Tom, whose last name is withheld so his wife doesn’t find out, to tell AskMen about masturbating to a stranger over Skype for the first time.

AskMen: I hear that you recently jerked off on webcam.

Tom: Well, I didn’t jerk off on a webcam, but through Skype, yes.

Who was it with?

Lucy, a 19-year-old sex worker I met [on a kinky message board].

And you’re married … no judgment, but does your wife know?

She doesn’t know about Lucy. We do have an open relationship, but choose not to share all the gory details. I think it would be bad if she knew about Lucy. I know, I’m disgusting.

Do you have Lucy tell you that you’re disgusting when you jerk off? What’s it like?

No, no, I’m not a sub. It’s just hot. She’s into it. She strips, teases me and touches herself. Then I get hard and blow a giant load — she loves it. That’s probably it. I like how into it she is. It feels good to know that a hot 19-year-old wants to watch you jerk off.

I’m paying her, of course, I know the rules. She deserves to be paid, and that makes it even hotter.

How did you discover that you liked when girls watched you jerk off?

I guess I fantasized about it. Jerking off gets a bad rap, people saying handjobs are for high schoolers and all that. Sex parties are cool, but the guy jerking off in the corner is the creep that no one wants to f*ck in front of. You’re basically a sexual predator jerking off in the park as children walk by.

Jerking off in front of others is very stigmatized. I do it with my wife every once in a while, but we mostly just f*ck.

How did you find Lucy? Is she your first webcam model?

I was on a website for kinky people, looking through the group for jerking off in front of others. We are a vibrant community. I met Lucy there and we arranged a Skype session. It’s not through a traditional cam site, but [it’s consensual] and I pay her.

How is it?

It’s awesome! It gives me life!

What advice would give to someone else curious about trying it?

Do it. It’s better than therapy.

Never Have I Ever: Cheated on Someone
The Most Common Kinks & Fetishes
What You Need to Know About Open Relationships

Source: AskMen